Synthesis of structure-defined conjugated polymers directly bound to porphyrins

Kenichi Oyaizu, Manabu Hoshino, Takuya Imai, Hidenori Murata, Makoto Yuasa

Research output: Chapter in Book/Report/Conference proceedingConference contribution

Abstract

5-(3-Thienyl)-10,15,20-triethyl-21H,23H-porphine was prepared by the ring closure of pyrrole and a 3:1 mixture of propionaldehyde and 3- thiophenecarbaldehyde. Oxidative polymerization of the porphyrin with typical oxidants such as FeCl3 gave a polythiophene derivative bearing porphyrins directly bound to the β-position of the main chain. The very bulky β-substituents allowed the polymerization to proceed regioselectively even at room temperature, resulting in the formation of the β-substituted polythiophene with an HT-HT content of more than 90%. The porphyrin substituents aligned cofacially along the main chain, which served as the catalytic site for the four-electron reduction of O2 to H2O (O2 + 4e- + 4H+ = 2H2O) when cobalt ions were introduced into the porphyrins. A novel platinum-free catalyst for the reduction of O2 for fuel cell cathodes, 1/CB (M = CoII), was thus prepared by the electropolymerization of the porphyrin at the surface of carbon black (CB), which reduced O2 with four electrons at more poritive potentials than the standard two-electron reduction potential of O2 to H2O2.

Original languageEnglish
Title of host publicationPolymer Preprints, Japan
Pages3030-3031
Number of pages2
Volume55
Edition2
Publication statusPublished - 2006
Externally publishedYes
Event55th Society of Polymer Science Japan Symposium on Macromolecules - Toyama
Duration: 2006 Sep 202006 Sep 22

Other

Other55th Society of Polymer Science Japan Symposium on Macromolecules
CityToyama
Period06/9/2006/9/22

Fingerprint

Conjugated polymers
Porphyrins
Carbon black
Electrons
Bearings (structural)
Polymerization
Electropolymerization
Polymers
Oxidants
Fuel cells
Platinum
Cobalt
Cathodes
Derivatives
Catalysts
Ions
Temperature

Keywords

  • Conjugated polymer
  • Electrode catalyst
  • Electron transfer
  • Polymer complex
  • Porphyrin

ASJC Scopus subject areas

  • Engineering(all)

Cite this

Oyaizu, K., Hoshino, M., Imai, T., Murata, H., & Yuasa, M. (2006). Synthesis of structure-defined conjugated polymers directly bound to porphyrins. In Polymer Preprints, Japan (2 ed., Vol. 55, pp. 3030-3031)

Synthesis of structure-defined conjugated polymers directly bound to porphyrins. / Oyaizu, Kenichi; Hoshino, Manabu; Imai, Takuya; Murata, Hidenori; Yuasa, Makoto.

Polymer Preprints, Japan. Vol. 55 2. ed. 2006. p. 3030-3031.

Research output: Chapter in Book/Report/Conference proceedingConference contribution

Oyaizu, K, Hoshino, M, Imai, T, Murata, H & Yuasa, M 2006, Synthesis of structure-defined conjugated polymers directly bound to porphyrins. in Polymer Preprints, Japan. 2 edn, vol. 55, pp. 3030-3031, 55th Society of Polymer Science Japan Symposium on Macromolecules, Toyama, 06/9/20.
Oyaizu K, Hoshino M, Imai T, Murata H, Yuasa M. Synthesis of structure-defined conjugated polymers directly bound to porphyrins. In Polymer Preprints, Japan. 2 ed. Vol. 55. 2006. p. 3030-3031
Oyaizu, Kenichi ; Hoshino, Manabu ; Imai, Takuya ; Murata, Hidenori ; Yuasa, Makoto. / Synthesis of structure-defined conjugated polymers directly bound to porphyrins. Polymer Preprints, Japan. Vol. 55 2. ed. 2006. pp. 3030-3031
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AB - 5-(3-Thienyl)-10,15,20-triethyl-21H,23H-porphine was prepared by the ring closure of pyrrole and a 3:1 mixture of propionaldehyde and 3- thiophenecarbaldehyde. Oxidative polymerization of the porphyrin with typical oxidants such as FeCl3 gave a polythiophene derivative bearing porphyrins directly bound to the β-position of the main chain. The very bulky β-substituents allowed the polymerization to proceed regioselectively even at room temperature, resulting in the formation of the β-substituted polythiophene with an HT-HT content of more than 90%. The porphyrin substituents aligned cofacially along the main chain, which served as the catalytic site for the four-electron reduction of O2 to H2O (O2 + 4e- + 4H+ = 2H2O) when cobalt ions were introduced into the porphyrins. A novel platinum-free catalyst for the reduction of O2 for fuel cell cathodes, 1/CB (M = CoII), was thus prepared by the electropolymerization of the porphyrin at the surface of carbon black (CB), which reduced O2 with four electrons at more poritive potentials than the standard two-electron reduction potential of O2 to H2O2.

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